N-Hydroxy-4-(7-chloro-2-methoxybenzo[b][1,5]naphthyridin-10-ylamino)benzamide

ID: ALA4750838

PubChem CID: 162652310

Max Phase: Preclinical

Molecular Formula: C20H15ClN4O3

Molecular Weight: 394.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2nc3cc(Cl)ccc3c(Nc3ccc(C(=O)NO)cc3)c2n1

Standard InChI:  InChI=1S/C20H15ClN4O3/c1-28-17-9-8-15-19(24-17)18(14-7-4-12(21)10-16(14)23-15)22-13-5-2-11(3-6-13)20(26)25-27/h2-10,27H,1H3,(H,22,23)(H,25,26)

Standard InChI Key:  RLHSWYLCHQWPQD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.9522  -24.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9522  -25.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575  -25.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6575  -24.3548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3627  -24.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3638  -25.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0681  -25.9901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0660  -24.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7748  -24.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797  -25.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4876  -25.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1952  -25.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1903  -24.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4779  -24.3497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0638  -23.5386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7704  -23.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4803  -23.5369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1848  -23.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1869  -22.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782  -21.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7675  -22.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8950  -21.9045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6023  -22.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8959  -21.0873    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6041  -20.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8960  -24.3453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6057  -24.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2464  -25.9933    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  1  4  1  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
  8 15  1  0
 15 16  1  0
 16 17  2  0
 16 21  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 19 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 13 26  1  0
 26 27  1  0
  2 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4750838

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 394.82

Molecular Weight (Monoisotopic): 394.0833

AlogP: 4.31

#Rotatable Bonds: 4

Polar Surface Area: 96.37

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.24

CX Basic pKa: 6.00

CX LogP: 4.00

CX LogD: 3.98

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.27

Np Likeness Score: -1.12

References

1. Tseng HJ,Lin MH,Shiao YJ,Yang YC,Chu JC,Chen CY,Chen YY,Lin TE,Su CJ,Pan SL,Chen LC,Wang CY,Hsu KC,Huang WJ.  (2020)  Synthesis and biological evaluation of acridine-based histone deacetylase inhibitors as multitarget agents against Alzheimer's disease.,  192  [PMID:32151835] [10.1016/j.ejmech.2020.112193]

Source

Source(1):

• Scientific Literature